Category Archives: Crossdressing

When you’re gay, it’s hard to talk to your parents about certain things. No matter how accepting or open-minded they may be, gay relationships, gay culture, and the mechanics of gay sex will stay a mystery to them — unless, of course, one of your parents is gay — or both.

Anyone who has been out of the closet for any amount of time knows that “gay” is more than a label to define your sexuality. It is a core part of your identity, and words like “queer,” “bi,” and “LGBTQ” constitute a significant part of your life — your people, your language, and your interests, both politically and socially. These words define a culture that our straight parents will never fully know. They may watch softened depictions of it on Modern Family, but they have never sung drunk karaoke at your favorite gay watering hole or queened out to Britney. They’ve never danced in a sea of sweaty men till 6 a.m. and they have no idea what Nasty Pig is.

Much of our culture can be hard to explain. Poppers and anal plugs will probably never warrant a conversation with mom, but other conversations — about PrEP and nonmonogamy, for example — can lead to greater understandings. Here’s a list of all those things gay men don’t talk about with their parents, with a small smattering of advice on how to do so!

1. Douching

The thought of you having sex with another man crossed your parents’ minds from the moment they found out you were gay. Though they would never admit it, they still wonder about it from time to time. The image flashes when they’re trying to go to sleep, when they’re taking the dog out for a walk. Like many straight people, they may be clueless as to how it all works and may mistakenly believe it to be a very messy business. But douching — the process of cleaning out the anal cavity before sex — is one of those off-limits topics, one I would never bring with to them.

One way to hint at it without having to say anything is to have your parents over to your place for a night where there is, regrettably, only one shower. You must conveniently forget to unscrew the metal douching hose from its attachment at the side of your shower head. I’m not saying you should picture your mother naked, but envision her standing in your shower, looking through your assortment of overpriced sugar scrubs, charcoal-infused body bars, and organic, woodsy-smelling shampoos, and frowning over that dangling hose with the phallic-shaped metal attachment at the end. Then, hopefully, it will click, and she’ll deduce that your sex is not quite as messy as she thought.

2. Poppers

When I’m talking to guys on Scruff whose profiles read “No PnP,” I usually ask, “Do you use poppers?” Most frequently, the answer is, “Sure. Love poppers.”

Poppers, while still a drug, are so mild that many gay men do not consider them in the same “sex drug” category that Tina (crystal meth) and G fall into. They’ve become staples of gay sex, gay culture, and gay history. We’ve been using them since the ’70s for their particular power of relaxing the anal sphincter for a few minutes, just long enough to get sex revved up. But if you try to explain the process of inhaling alkyl nitrites — video head cleaner — to your parents, they will likely conjure the imagine of junkies snorting glue in the school supplies aisle.

As with many items on this list, you could make the reasonable argument that poppers — like most facets of gay sex — never need to be brought up to your parents, since your sex life is not any of their business. But if they ever wonder why you have a few small amber bottles of some chemical that smells like nail polish in the freezer, poppers may inadvertently become a discussion topic in the kitchen.

3. Fisting

Even if you don’t do it, you know someone who does. Fisting has long lost its shock value in gay circles, and has crossed over from dark sex dungeons into the arena of mainstream gay life. Many guys who aren’t regularly seen in leather harnesses now enjoy fisting. But imagine explaining to Dad how some guys take hands (and more) up the anus — especially when the idea of taking an erect penis up there is already outside the realm of his imagination. Many people, gay and straight, do not believe — or have not accepted — that fisting, when done safely and correctly, does not create long-term damage and can be an incredibly passionate and enjoyable sexual experience.

4. Drag

Even though words like “slay” and “werq” have broken into the straight lexicon — primarily thanks to RuPaul’s Drag Race — the art and culture of drag is still a queer creation and belongs to us. Straight people are welcome to enjoy drag shows at their local gay bar, so long as they tip, but theirs is not a history of disenfranchisement and oppression, abuse and homelessness, poverty and sex work — a queer history in which drag emerged as an act of self-empowerment.

Drag can be hard to explain to your parents. It was hard to explain to mine. My parents assumed that all gay men dress up in women’s clothes and sing diva power ballads, so the concept of drag was indistinguishable from the rest of gay life to them. They could not appreciate drag’s cultural importance because it’s not their culture, and they did not understand its complicated history with the transgender movement because they do not understand, and refuse to understand, the concept of transgender identity.

To them, as well as to many others, drag artists and trans people are the same thing — a deeply incorrect assumption that has led to something of a modern cultural rift between trans activists and the drag world. The two camps have an overlapped history, since many trans folks first discovered their true identities through drag. In the ’60s, ’70s, and ’80s, when the concept of “transgender” was not as developed as it is today, many transgender people could only express themselves through drag art. As our cultural understandings both of drag and transgender identity have evolved, the two have split, and the burden has fallen on many transgender folks and trans activists to highlight and explain the significant difference between the two. Many people, my parents included, consider a trans woman to be “a man in a dress” — essentially a drag performer — and the phrase has become a terribly offensive slur against transgender women.

Take your parents to a drag show. Give them bills to tip the queens. (This assumes that your parents, unlike mine, are wiling to set foot in a gay bar.) Let them see drag in all its ferocity and kitschy wonder, then afterward, walking home, highlight the fact that what they saw was performance art, a toss-up between cabaret and camp. Explain to them that even if a transgender person does drag, the drag is the performance, but their trans identity is not. Regardless of what someone does onstage, transgender identity is a person’s authentic identity. “While drag is done for an audience, coming out as transgender is done solely for oneself,” a trans friend once told me. “And it is just as healthy and important to do as any coming-out, any form of self-acceptance that your mental health depends on.”

5. Bears, Otters, and Pups, Oh My!

The labels will be the bane and the delight of your gay life. Gay men have long established the bizarre practice of defining and stereotyping ourselves into labels based on body type and sex practices. In the gay lexicon, burly, hairy men over a certain age are “bears.” Young bears are “cubs.” Skinnier, scruffier guys are “otters.” Young, lean, hairless guys are “twinks.” Guys into puppy play (a kink scene that was listed on my list of 30 kinky terms every gay man should know) who enjoy the “pup” role are “pups,” both in and out of the scene. Guys who prefer condomless sex are “pigs.” Tall, skinny gay guys are “giraffes” (a lesser-known label).

How did we come up with these? Regardless of where they came from, and in spite of their much-debated value, the labels are likely here to stay. While they are common parts of our speak, your parents would probably be confused to learn that you think bears are sexy or that your boyfriend is a puppy.

6. Nonmonogamy

Nonmonogamy works out for gay men. In fact, this writer believes that nonmonogamous pairings, open and semi-open relationships, and relationships with relaxed sexual parameters are ideal for us — much more so than the monogamous alternative. The concept of nonmonogamy may seem foreign to our parents. Having a frank conversation about the parameters of your particular gay relationship with your parents may be awkward, but it can lead to something good. Explaining the distinction between sex and love may not leave everyone in agreement, especially if your parents are religious, conservative, or both. But at the very least, it will be an illuminating window into your life.

7. HIV

Gay men are still disproportionately affected by HIV compared to our straight counterparts. While no one needs to come out as HIV-positive, least of all to their parents, many poz gay men choose to do so at some point, for various reasons. Coming out to my parents about my status was hard; I did it the same morning an op-ed I wrote about coming out as poz was published in The Advocate last December.

Many of our parents remember the early days of the AIDS epidemic, so the news can be hard for them. They may mistakenly believe that the outlook for an HIV-positive person in 2016 is the same as it was 30 years ago. Most well-informed gay men, particularly those who live in urban areas, are up to speed on modern HIV care and know that with antiretroviral treatment, HIV has become a livable chronic illness that is more preventable today than ever before. Our parents aren’t accustomed to seeing testing trucks outside of gay clubs or HIV pamphlets disseminated in chic gayborhoods, so they will probably need some information to alleviate the initial fear. Give them resources and time.

8. PrEP

There may never be a need to talk about your once-daily Truvada pill to your parents, but if they see the medicine bottle by the sink one day when the family is sharing a beach condo, you need to have answers ready.

PrEP is the once-a-day pill regimen for HIV-negative people that has proven extremely effective at preventing HIV transmission. Statistically, it’s more reliable than regular condom use. Upon initial explanation, your parents will likely respond the way many have responded to PrEP and see it as an excuse to have raucous unprotected sex. Even if you are having raucous condomless sex, you will have to explain to them that you are still protected from HIV.

9. Top/Bottom

Just as your parents have been envisioning your sex from the moment they first learned you were gay, they have been wondering “what you do.” When/if they meet your boyfriend, they will wonder “what he does.” They won’t say it aloud, but they wonder, late at night, after the dinner dishes have been put away, whether you’re the top or the bottom. (I always find it remarkable how straight people assume every gay man is one or the other — versatile guys don’t exist in straight visions of gay sex.)

Like douching, this is one I will never talk about to my parents, no matter how chummy we get.

10. Kink

My parents know I am gay. They know I am having sex. They know I date and have sex with other men. But they do not know and will not be told how much I love having used underwear stuffed in my mouth and my wrists tied together with duct tape. The only time I ever came close to explaining my kink practices was at the beach a few years ago when I realized there were still red caning lines on my butt and legs. I lay in the tanning bed to darken the skin around the marks and opted for a pair of baggier, less flattering board shorts.

While kink is not restricted to gay men, we have certainly been longtime practitioners of the rougher arts. Like drag, leather was originally our thing and has by and large remained so. Kink and fetish play are things that gay men of all stripes can at least be familiar with, and have probably dabbled in at one time or another. But it is one area of gay life that our parents may have a hard time distinguishing from rape and abuse, perversion and degeneracy. Explaining it can be tough.

Its accouterments can be hard to hide — all those ass toys and leather gear require storage, and that sling in the bedroom cannot reasonably be disguised as a place to hang laundry. Have a regimen prepared for surprise visits and dinners, and if you enjoy getting backlashes or caning down your legs, try not to do so before a family beach trip.

Name: ANGELO
Gender: Male
Age: 49
Location: NEW YORK
Hi I heard you on the playboy channel the other day; it was great. I’m married and like wearing women’s clothes mostly panties and stockings. My wife knows this and is OK with it. I also like when we role reverse and she penetrates my anus do u think this is all OK?

Yeah, Angelo, I think it’s all fine. Cross-dressing and role reversal role-play are common enough fetishes. You’re very fortunate to have a wife who will join you in your kink. Lucky you and, more importantly, good for her!

Here’s what I want you to do. Go to your wife and tell her you love her and thank her profusely for being so accommodating by indulging you your behavior. Tell her you want to do something special for her to show your appreciation. Ask her what she wants or needs and fulfill that request ASAP.

My sense is that few of us show enough gratitude to our loving, obliging and compliant partners or as we ought. The world is full of unhappy and unfulfilled people, so if we’ve hit the jackpot we really need to reward the ones who love us and fuck us as we are.

Name: Astrit
Gender: Male
Age: 20’s
Hi there. I have question about anal douching.
I’m in my early twenties and see myself as being a reasonable healthy young gay man. I’ve recently gotten into anal douching and, to my surprise, found that I really like it a lot. This is partly because the thought of being clean really appeals to me. Now I’m wondering how frequently I can safely do it and what kind of precautions I should take. Is it safe to go with just pure water for douching? Is there any risk in doing it more than once or twice a week? Would it be worth it?

I’ve written and talked about anal douching extensively on my site. You can find postings and podcasts containing the subject by using this site’s search function in the sidebar to your right. Type in ANAL DOUCHE and presto!

You can also use the category pull down menu. Look under Anal; there’s a subcategory labeled anal-douche.

Here’s the kind of information you will find: Warm water is all you need. Soap is recommended for cleaning outside your hole, but ever use soap up in your hole.

Some men add lemon juice or vinegar (1-2 Tbs. per quart) of the warm water. Others dissolve (2 Tbs.) of baking soda in a quart of warm water.

Stay away from commercially produced douches; most contain harmful and irritating chemicals. And trust me, you don’t want that. Besides, all those over the counter douches are expensive. And all that packaging is definitely not eco-friendly. And we all want to be green perverts, don’t we?

Finally there is always the ever-versatile shower or bath bidet option. You can find one model, the Perfect Fit Ergoflo Extra on the Perfect Fit website along with all their other outstanding products. And, since it looks like you’re a budding douche fetishist, you might consider the Deluxe Shower Bidet, which can be found in Dr Dick’s Stockroom. Look for the My Stockroom banner in the sidebar to your right. This is a stainless steel option that hooks up to your shower head.

Here’s something unusual. Just last month we heard from Roxie, a crossdresser at a crossroads. Today, another crossdresser. That’s what’s so unusual, two in one month. Maybe it’s something in the stars. Anyway, our fabulous friend here has a bit of the ennui.

Name: Mariah
Gender: Male
Age: 23
Location: Brewster NY
I have been doing a lot of crossdressing secretly and I have no idea how to stop. Its been going on for quite a number of years and I am not sure exactly what I should do. I enjoy a lot of other things that I won’t mention. I guess my question is how long does it take to get over this?

Mariah darling, I’m confused. You’ve been secretly crossdressing for a number of years and now you want to stop? Why? Sounds to me like you’re still into it. A lot!

And then you tantalize me with; “I enjoy a lot of other things that I won’t mention.” What’s up with that?

So ok, you’re a kinky little transvestite; is that such a big deal? Crossdressing is a relatively innocuous fetish, as far as fetishes go. And if you’ve been doing it for years, albeit secretly, I’d guess you have your fetish under control. It doesn’t sound like it’s messin’ with or spillin’ over into the rest of your life. So again, my question is, why stop?

If you’re just bored with it, which doesn’t sound like the case; why not simply pack up your frilly knickers and dancer heels and drop them off at the Goodwill? If you don’t have women’s clothing around the house, you won’t be able to crossdress. So that part is relatively simple.

Georgina

However, getting over a fetish is not so easy as ridding yourself of your frocks. There’s probably a psychological and an erotic hook in your crossdressing, as there is for most folks who do drag. After all, this is what makes the whole exercise a turn on and so much fun. You can learn to wean yourself off this activity, if you really, really want to. But again my question is: why?

If you feel your crossdressing is screwin’, up your life, or contaminating your relationships; well, that’s another thing. But you don’t say that. Maybe you just need some assistance in understanding what’s going on with you and some support from others like you. And that, my dear Mariah, is very easy to come by. First, let me direct you to a couple of brilliant podcast interviews I’ve done with two amazing crossdressers — first, Debra Christina Darling. (You’ll find Part 1 of that conversation HERE and Part 2HERE!) Then there’s the toast of the Emerald City, Sylvia O’Stayformore. (You’ll find Part 1 of that conversation HERE and Part 2HERE!). Or just use the the search function in the sidebar to your right, type in either of those names, and PRESTO! Faster than you can say Lane Bryant, you be taken to their podcast postings.

These interviews are chock full of information about crossdressing; the dos and don’t as well as the whys. I’ve also supplied a short list of online resources for crossdressers, drag queens, and transgender folk.